135192-53-9

Basic information

• Product Name: PENTAFLUOROPHENYL CHLOROTHIONOFORMATE
• Synonyms: CHLOROTHIOFORMIC ACID O-PENTAFLUOROPHENYL ESTER;O-PERFLUOROPHENYL CHLOROTHIOFORMATE;PENTAFLUOROPHENYL THIONOCHLOROFORMATE;PENTAFLUOROPHENYL CHLOROTHIONOFORMATE;PENTAFLUOROPHENYL CHLOROTHIONOFORMATE, 9 6%;PENTAFLUOROPHENYL CHLOROTHIONOFORMATE 97+%;Carbonochloridothioic acid, O-(pentafluorophenyl) ester;Chlorothioformic Acid O-Pentafluorophenyl Ester Pentafluorophenyl Thionochloroformate O-Perfluorophenyl Chlorothioformate
• CAS NO: 135192-53-9
• Molecular Formula: C₇ClF₅OS
• Molecular Weight: 262.58
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds
• Mol File: 135192-53-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 98-102 °C50 mm Hg(lit.)
• Flash Point: 189 °F
• Appearance: Solid
• Density: 1.635 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.03mmHg at 25°C
• Refractive Index: n20/D 1.481(lit.)
• CAS DataBase Reference: PENTAFLUOROPHENYL CHLOROTHIONOFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAFLUOROPHENYL CHLOROTHIONOFORMATE(135192-53-9)
• EPA Substance Registry System: PENTAFLUOROPHENYL CHLOROTHIONOFORMATE(135192-53-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 135192-53-9(Hazardous Substances Data)

Usage

Uses

Pentafluorophenyl chlorothionoformate may be used:as derivatizing agent during radical-chain deoxygenations of primary alcoholsas a reagent during the conversion of ribonucleoside to arabinonucleosidesas reagent during the conversion of 6,8-diethyl-7-hydroxy-5-propyl-hexahydro-indolizin-3-one to O-6,8-diethyl-octahydro-3-oxo-5-propylindolizin-7-yl benzothioate

InChI:InChI=1/C7ClF5OS/c8-7(15)14-6-4(12)2(10)1(9)3(11)5(6)13

Upstream product

• 463-71-8 thiophosgene 
• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 75-15-0 carbon disulfide 

Downstream Products

• 174579-29-4 Thiocarbonic acid O-{4-[bis-(2-chloro-ethyl)-amino]-phenyl} ester O-pentafluorophenyl ester 
• 352422-94-7 (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-pentafluorophenoxythiocarbonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene 
• 144752-19-2 O-cyclododecyl-O'-(2,3,4,5,6-pentafluorophenyl) thionocarbonate 
• 140479-90-9 tetradecyl (pentafluorophenyl)thionocarbonate 
• 140479-91-0 octadecyl pentafluorophenylthionocarbonate 

Relevant articles and documents

Bare-minimum fluorous mixture synthesis of a stereoisomer library of 4,8,12-trimethylnonadecanols and predictions of NMR spectra of saturated oligoisoprenoid stereoisomers

All four diastereomers of a typical saturated oligoisoprenoid, 4,8,12-trimethylnonadecanol, are made by an iterative three-step cycle with the aid of traceless thionocarbonate fluorous tags to encode configurations. The tags have a minimum number of total fluorine atoms, starting at zero and increasing in increments of one. With suitable acquisition and data processing, each diastereomer exhibits characteristic chemical shifts of methyl resonances in its 1H and 13C NMR spectra. Together, these shifts provide a basis to predict the appearance of the methyl region of the spectrum of every stereoisomer of higher saturated oligoisoprenoids.

The Invention of Radical Reactions. Part XXI. Simple Methods for the Radical Deoxygenation of Primary Alcohols.

Novel radical-chain deoxygenations of primary alcohols are described.The alcohols are acylated with the reagents pentafluorophenyl chlorothionoformate, 2,4,6-trichlorophenyl chlorothionoformate and 4-fluorophenyl chlorothionoformate and the intermediate thionocarbonates are deoxygenated with tributyltin hydride, triphenylsilane, diphenylsilane or phenylsilane in high-yielding reactions.Key Words: Thionocarbonates, Tributyltin hydride, Triphenylsilane, Diphenylsilane, Phenylsilane, Radical deoxygenations.